Massachusetts General Laws Part I. Administration of the Government (Ch. 1-182) Ch. 127, § 165

The superintendent or keeper of a jail or house of correction may, with the approval of the county commissioners, expend such amount, not exceeding twenty-five dollars, in aiding a prisoner discharged from his custody as in his opinion will assist such prisoner in his endeavor to reform. He may in his discretion pay it to the prisoner, or to some person selected by the superintendent or keeper, to be expended by him in behalf of the prisoner or for providing the prisoner with board, clothing, transportation or tools. The amount so paid by a superintendent or keeper shall be allowed and paid by the county like other prison expenses.